JP6196328B2 - 皮膚疾患を治療するためのホルミルペプチド受容体2アゴニストの使用 - Google Patents
皮膚疾患を治療するためのホルミルペプチド受容体2アゴニストの使用 Download PDFInfo
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- JP6196328B2 JP6196328B2 JP2015561540A JP2015561540A JP6196328B2 JP 6196328 B2 JP6196328 B2 JP 6196328B2 JP 2015561540 A JP2015561540 A JP 2015561540A JP 2015561540 A JP2015561540 A JP 2015561540A JP 6196328 B2 JP6196328 B2 JP 6196328B2
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EP (1) | EP2964214A1 (fr) |
JP (4) | JP6196328B2 (fr) |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2016529235A (ja) * | 2013-07-16 | 2016-09-23 | アラーガン、インコーポレイテッドAllergan,Incorporated | ホルミルペプチド受容体モジュレーターとしてのn−尿素置換アミノ酸の誘導体 |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2012329098B2 (en) | 2011-10-26 | 2017-08-03 | Allergan, Inc. | Amide derivatives of N-urea substituted amino acids as formyl peptide receptor like-1 (FPRL-1) receptor modulators |
CN104302630A (zh) * | 2012-04-16 | 2015-01-21 | 阿勒根公司 | 作为甲酰肽受体2调节剂的(2-脲基乙酰氨基)烷基衍生物 |
MA37618B1 (fr) | 2012-05-16 | 2017-08-31 | Actelion Pharmaceuticals Ltd | Dérivés pontés fluorés de spiro[2.4]heptane en tant qu'agonistes de récepteur alx |
US9284288B2 (en) | 2012-05-16 | 2016-03-15 | Actelion Pharmaceuticals Ltd. | 1-(p-tolyl) cyclopropyl substituted bridged spiro[2.4]heptane derivatives as ALX receptor agonists |
CN107312039B (zh) | 2012-08-30 | 2019-06-25 | 江苏豪森药业集团有限公司 | 一种替诺福韦前药的制备方法 |
CA2899804A1 (fr) * | 2013-03-06 | 2014-09-12 | Allergan, Inc. | Utilisation d'agonistes du recepteur 2 de peptide formyle pour le traitement de maladies dermatologiques |
AR096686A1 (es) | 2013-06-25 | 2016-01-27 | Actelion Pharmaceuticals Ltd | Derivados de espiro[2.4]heptano puenteados sustituidos con difluoroetil-oxazol como agonistas del receptor de alx |
RU2016105310A (ru) | 2013-07-18 | 2017-08-23 | Актелион Фармасьютиклз Лтд | Пиперазин-замещенные мостиковые производные спиро[2.4]гептана в качестве агонистов alx рецептора |
AR097279A1 (es) | 2013-08-09 | 2016-03-02 | Actelion Pharmaceuticals Ltd | Derivados de benzimidazolil-metil urea como agonistas del receptor de alx |
WO2015116566A1 (fr) * | 2014-01-29 | 2015-08-06 | Allergan, Inc. | Dérivés de 2,5-dioxoimidazolidin -1-yl -3-urée en tant que modulateurs de peptide formylé |
US9663457B2 (en) | 2014-04-09 | 2017-05-30 | Allergan, Inc. | Carbamoyl hydrazine derivatives as formyl peptide modulators |
EP3145916B1 (fr) | 2014-05-21 | 2020-02-12 | Allergan, Inc. | Dérivés d'imidazole en tant que modulateurs des récepteurs de peptide formylé |
MX2018006635A (es) * | 2015-12-10 | 2018-08-01 | Squibb Bristol Myers Co | Agonistas del receptor 2 de formilpeptido y del receptor 1 de formilpeptido, de piperidinona. |
CN109715602A (zh) | 2016-03-28 | 2019-05-03 | 阿勒根公司 | 苯基脲衍生物作为n-甲酰肽受体调节剂 |
EP3442950A1 (fr) * | 2016-04-12 | 2019-02-20 | Allergan, Inc. | Dérivés de phénylurée servant de modulateurs des récepteurs des peptides n-formyles |
RU2768587C2 (ru) * | 2016-10-06 | 2022-03-24 | Дайити Санкио Компани, Лимитед | Производное мочевины |
GB2561540A (en) * | 2017-03-13 | 2018-10-24 | Nodthera Ltd | Chemical compounds |
ES2799098B2 (es) * | 2019-06-10 | 2021-12-10 | Univ Madrid Carlos Iii | Aptameros agonistas del receptor fpr2 y usos de los mismos |
Family Cites Families (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4521210A (en) | 1982-12-27 | 1985-06-04 | Wong Vernon G | Eye implant for relieving glaucoma, and device and method for use therewith |
JPS63232846A (ja) | 1987-03-20 | 1988-09-28 | Haruo Ogura | 新規な固定相担体 |
AU6909300A (en) * | 1999-08-20 | 2001-03-19 | Merck & Co., Inc. | Substituted ureas as cell adhesion inhibitors |
DE10005275A1 (de) * | 2000-02-07 | 2001-08-09 | Bayer Ag | Neuartige Glycokonjugate |
EP1162194A1 (fr) | 2000-06-06 | 2001-12-12 | Aventis Pharma Deutschland GmbH | Dérivés de (thio)-urée inhibiteurs du facteur VIIa, procédé de leur préparation et leur utilisation |
DE10063008A1 (de) | 2000-12-16 | 2002-06-20 | Merck Patent Gmbh | Carbonsäureamidderivate |
US20060160856A1 (en) * | 2002-09-05 | 2006-07-20 | Dahl Bjarne H | Diarylurea derivatives and their use as chloride channel blockers |
US7576206B2 (en) | 2003-08-14 | 2009-08-18 | Cephalon, Inc. | Proteasome inhibitors and methods of using the same |
JP4769082B2 (ja) | 2003-12-17 | 2011-09-07 | 武田薬品工業株式会社 | ウレア誘導体、その製造法及び用途 |
WO2006065755A2 (fr) | 2004-12-13 | 2006-06-22 | Glaxo Group Limited | Sels d'ammonium quaternaire d'amines heteroaromatiques fusionnees utilises comme nouveaux antagonistes du recepteur de l'acetylcholine muscarinique |
WO2007076055A2 (fr) * | 2005-12-22 | 2007-07-05 | Entremed, Inc. | Compositions et methodes comprenant l'utilisation d'antagonistes du recepteur active par des proteases |
KR20090121832A (ko) * | 2008-05-23 | 2009-11-26 | 인제대학교 산학협력단 | 2-(2-히드록시벤조일)히드라진카르복시아미드 유도체 또는이의 약학적으로 허용가능한 염, 이의 제조방법, 및 이를유효 성분으로 함유하는 선택적 면역 억제용 약학적 조성물 |
AU2009314165B2 (en) * | 2008-11-11 | 2014-05-15 | Signum Biosciences, Inc. | Isoprenyl compounds and methods thereof |
KR20100101054A (ko) * | 2009-03-07 | 2010-09-16 | 주식회사 메디젠텍 | 세포핵에서 세포질로의 gsk3의 이동을 억제하는 화합물을 함유하는 세포핵에서 세포질로의 gsk3 이동에 의해 발생되는 질환의 치료 또는 예방용 약학적 조성물 |
EP2585054A1 (fr) * | 2010-06-24 | 2013-05-01 | Allergan, Inc. | Dérivés d'acides cycloalkyl- et cycloalcényl-1,2-dicarboxyliques présentant une activité agoniste ou antagoniste du récepteur fprl-1 |
EP2646030A1 (fr) * | 2010-12-03 | 2013-10-09 | Allergan, Inc. | Compositions pharmaceutiques comprenant des dérivés de la 3,4-dihydro-isoquinoléin-2(1h)-yl-3-phénylurée présentant une activité d'agoniste ou d'antagoniste de l'analogue-1 du récepteur des peptides formylés (fprl-1) |
WO2012109544A1 (fr) | 2011-02-11 | 2012-08-16 | Allergan, Inc. | Nouveaux dérivés de 1-(1-oxo-1,2,3,4-tétrahydroisoquinolin-7-yl)urée en tant que modulateurs du récepteur de type 1 de n-formyl peptide (fprl-1) |
US8653299B2 (en) | 2011-03-17 | 2014-02-18 | Allergan, Inc. | Dihydronaphthalene and naphthalene derivatives as N-formyl peptide receptor like-1 (FPRL-1) receptor modulators |
WO2012174243A1 (fr) | 2011-06-17 | 2012-12-20 | Allergan, Inc. | D-sérine dans le traitement des troubles du système visuel |
EP2731931A1 (fr) * | 2011-07-11 | 2014-05-21 | Allergan, Inc. | Dérivés polycycliques de pyrrolidine-2,5-dione en tant que modulateurs du récepteur fprl-1 (récepteur de n-formyl peptide de type 1) |
AU2012329098B2 (en) * | 2011-10-26 | 2017-08-03 | Allergan, Inc. | Amide derivatives of N-urea substituted amino acids as formyl peptide receptor like-1 (FPRL-1) receptor modulators |
US8492556B2 (en) * | 2011-11-10 | 2013-07-23 | Allergan, Inc. | 2,5-Dioxoimidazolidin-1-yl-3-phenylurea derivatives as formyl peptide receptor like-1 (FPRL-1) receptor modulators |
US8541577B2 (en) * | 2011-11-10 | 2013-09-24 | Allergan, Inc. | Aryl urea derivatives as N-formyl peptide receptors like-1 (FPRL-1) receptor modulators |
EP2814815A1 (fr) | 2012-02-16 | 2014-12-24 | Allergan, Inc. | Dérivés d'imidazolidine-2,4-dione en tant que modulateurs du récepteur des peptides n-formylés 2 |
CN104302630A (zh) * | 2012-04-16 | 2015-01-21 | 阿勒根公司 | 作为甲酰肽受体2调节剂的(2-脲基乙酰氨基)烷基衍生物 |
CA2899804A1 (fr) * | 2013-03-06 | 2014-09-12 | Allergan, Inc. | Utilisation d'agonistes du recepteur 2 de peptide formyle pour le traitement de maladies dermatologiques |
KR102290134B1 (ko) * | 2013-03-06 | 2021-08-17 | 알러간, 인코포레이티드 | 안구 염증성 질환을 치료하기 위한 포르밀 펩타이드 수용체 2의 작용제의 용도 |
US9428549B2 (en) * | 2013-07-16 | 2016-08-30 | Allegran, Inc. | Derivatives of N-urea substituted amino acids as formyl peptide receptor modulators |
WO2015042071A1 (fr) | 2013-09-19 | 2015-03-26 | Allergan, Inc. | Dérivés de diphénylurée servant de modulateurs des récepteurs des peptides formylés |
RU2703725C1 (ru) | 2013-11-21 | 2019-10-22 | Аллерган, Инк. | Производные фенилкарбамата в качестве модуляторов формилпептидного рецептора |
EP3145916B1 (fr) * | 2014-05-21 | 2020-02-12 | Allergan, Inc. | Dérivés d'imidazole en tant que modulateurs des récepteurs de peptide formylé |
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Cited By (1)
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JP2016529235A (ja) * | 2013-07-16 | 2016-09-23 | アラーガン、インコーポレイテッドAllergan,Incorporated | ホルミルペプチド受容体モジュレーターとしてのn−尿素置換アミノ酸の誘導体 |
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